"Last ride" strongly suggests death, even without any allusion to earlier texts. If it were just the last ride for its particular purpose, the title would be inappropriate. Casey Jones was a hero, Hobo Bill a poor victim, both die before the respective song is over.

I have the strong feeling that we are missing some existing additional information to shed light on the obscure details. One of the keys may be found in the London Underground of that time.

(Suicide by self-electrocution on the rails is a risky endeavour; most seem to fail - but KK might not have known this, in pre-Google times.)